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Rebecca Dale, dear lovely, loving and loved wife of my broken-hearted brother Andy, and mother of their two wonderful children, died early Saturday morning.

This time last week I arrived in Berkeley, CA to support my brother Andy and his two children. It was the birthday of Rebecca, Andy's wife of 17 years. In the early hours of Saturday morning, Rebecca passed peacefully and gently from this world, lying in her bed at home, with her family present, after what she called her ten year dance with cancer.

At the MassTLC Innovation UnConference in October 2009 I got a nod from Scott Kirsner, technology columnist from the Boston Globe, who included my session as one of the five best session titles.

The session is titled “All the Bad Things VCs want to do to You!”. In it I talk about many of the principles behind Venture Capital investment terms, and do so starting with the most negative view. This provides a jumping off point that the entrepreneurs can relate to (who doesn’t love to hate “vulture capitalists”?), and makes it compelling (or at least amusing). The session allows me to get into the core idea that no-one should take a VC investment unless the the deal on the table is still compelling relative to what you give up (time, ownership, control … and more!).

Back in 2009 the session went very well. At the end, one of the participants introduced himself as a lawyer working with start-ups and told me he had come to the session to make sure I really was going to be honest about VC behavior. He confirmed, indeed, I was.

Since then I have repeated the session in various incubator, business school and conference settings. Each session is different, based on the questions and interests of the audience, although I always start with the same theme: “VCs just want four things from you: your ideas, your time, lots of ownership in your company and control!”

As I have quoted before, Paul Gompers of HBS succinctly notes that management is the optimization of resources and entrepreneurship is the optimization of opportunity. Optimizing resources is tough enough, and you can generally count your resources. Optimizing opportunity is fraught with uncertainty, starting with characterizing (let alone quantifying) what the opportunity really is. Entrepreneurship, and startup investing, operates in a field of uncertainty, often massive uncertainty.

Many others have written about how to manage that uncertainty, and I can say, with certainty, that even the good articles do not reduce uncertainty. At best they clarify that any decision is better than none, and send you out to test hypotheses, find failure through controlled experimentation and generally do more faster.

I don’t think I am adding deeply to the field of uncertainty studies with this posting, but here are a couple of interesting quotes and my own comments.

I can’t find the source of the quote “confusion is a prelude to clarity” (though you can buy the t-shirt), but it brings to mind the most unlikely seeker of uncertainty, Alfred Sloan. Sloan was the legendary CEO of General Motors and is credited with being one of the fathers of modern management. When chairing a board meeting in which an important issue was being discussed, Sloan said “Gentlemen, I take it we are all in complete agree­ment on the decision here . . . Then I propose we postpone further discussion of this matter until our next meeting to give ourselves time to develop disagreement and perhaps gain some understanding of what the decision is all about.” (Note: sources differ on the exact wording.)

Another great quote, which I hesitate to admit I first read in a Tom Clancy book, is “no plan survives contact with the enemy” (Helmuth von Moltke). I prefer the variant “no plan survives contact with the enemy and no battle was won without a plan.”

The conclusions are unsurprising for those in the startup world, but intriguing coming from regimented management practitioners and military minds: embrace and seek uncertainty, expect uncertainty, prepare for uncertainty.

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